The nuclear factor-KB （NF-KB） transcription factors control many physiological processes including in- flammation, immunity, apoptosis, and angiogenesis. In our search for NF-KB inhibitors from natural resources, we...The nuclear factor-KB （NF-KB） transcription factors control many physiological processes including in- flammation, immunity, apoptosis, and angiogenesis. In our search for NF-KB inhibitors from natural resources, we identified 4＇,6-dihydroxy-4-methoxyisoaurone （ISOA） as an inhibitor of NF-KB activation from the seeds of Tricho- santhes kirilowii. However, the mechanism by which ISOA inhibits NF-KB activation is not fully understood. In the present study, we demonstrated the effect of ISOA on NF-KB activation in TNF-α-stimulated HeLa cells. This com- pound suppressed NF-KB activation through the inhibition of IKB kinase （IKK） activation. ISOA also has an influ- ence on upstream signaling of IKK through the inhibition of expression of adaptor proteins, TNF receptor-associated factor 2 （TRAF2） and receptor interacting protein 1 （RIP1）. Consequently, ISOA blocked the phosphorylation and degradation of the inhibitor of NF-KB alpha （IKBα） , and subsequent phosphorylation and nuclear translocation of p65. The suppression of NF-KB activation by ISOA led to the down-regulation of target genes involved in inflam- mation, proliferation, angiogenesis and invasion, as well as potentiation of TNF-α-induced apoptosis at least in part through activation of caspase-8. Taken together, this study extends our understanding on the mechanisms underly- ing the anti-inflammatory and anti-cancer activities of ISOA. Our findings provide new insight into the molecular mechanisms and a potential application of ISOA for inflammatory diseases as well as certain cancers associated with abnormal NF-KB activation.展开更多
Cultivation of an endophytic fungus Aspergillus niger EN-13 that was isolated from the inner tissue of the marine brown alga Colpomenia sinuosa resulted in the characterization of a new naphthoquinoneimine derivative,...Cultivation of an endophytic fungus Aspergillus niger EN-13 that was isolated from the inner tissue of the marine brown alga Colpomenia sinuosa resulted in the characterization of a new naphthoquinoneimine derivative, namely, 5,7-dihydroxy-2-[1-（4- methoxy-6-oxo-6H-pyran-2-yl）-2-phenylethylamino]-[ 1,4]naphthoquinone. The structure of the new compound was established on the basis of various NMR spectroscopic analyses including 2D NMR techniques, El-MS, and HR-ESI-MS. This compound displayed moderate antifungal activity.展开更多
Two hydrates of sodium 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Na(H2O)](C17H13O6SO3)2H2O, 1) and nickel 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Ni(H2O)6](C17H13O6SO3)24H2O, ...Two hydrates of sodium 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Na(H2O)](C17H13O6SO3)2H2O, 1) and nickel 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Ni(H2O)6](C17H13O6SO3)24H2O, 2) were syn-thesized and characterized by IR, 1H NMR and X-ray diffraction analyses. The hydrate 1 crystallizes in the mono-clinic system, space group P2(1) with a=0.8201(9) nm, b=0.8030(8) nm, c=1.5361(16) nm, =102.052(12), V=0.9893(18) nm3, Dc=1.579 g/cm3, Z=2, =0.252 nm-1, F(000)=488, R=0.0353, wR=0.0873. The hydrate 2 belongs to triclinic system, space group P-1 with a=0.7411(3) nm, b=0.8333(3) nm, c=1.7448(7) nm, a=86.361(6), 撸?6.389(5), ?=88.999(3), V=1.0731(7) nm3, Dc=1.587 g/cm3, Z=1, =0.649 mm-1, F(000)=534. In the structure of 1, the sodium cation is coordinated by six oxygen atoms and two adjacent ones are bridged by three oxygen atoms to form an octahedron chain. The C—H…p hydrogen bonds exist between two isoflavone molecules in the structure of 2. Meanwhile, hydrogen bonds in two compounds, link themselves to assemble two three-dimensional network structures, respectively.展开更多
A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots o...A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.展开更多
A new alkaloid, named 6-（2＇,3＇-dihydroxy-4＇-hydroxymethyl-tetrahydro-furan-1＇-yl）cyclopentadiene[c]pyrrole-1,3-diol, was isolated from the seeds of Castanea mollissima Blume. The structure was elucidated based o...A new alkaloid, named 6-（2＇,3＇-dihydroxy-4＇-hydroxymethyl-tetrahydro-furan-1＇-yl）cyclopentadiene[c]pyrrole-1,3-diol, was isolated from the seeds of Castanea mollissima Blume. The structure was elucidated based on spectroscopic evidence including 2D NMR techniques.展开更多
Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Dr...Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.展开更多
A convenient and stereoselective approach to the synthesis of(3S. 4R. 6S)- 2-oxo-3, 4-dihydroxy-6-methyl-octanate derivative, a key intermediate for the synthesis of HIV-1 protease inhibitor of didemnaketals analogue,...A convenient and stereoselective approach to the synthesis of(3S. 4R. 6S)- 2-oxo-3, 4-dihydroxy-6-methyl-octanate derivative, a key intermediate for the synthesis of HIV-1 protease inhibitor of didemnaketals analogue, has been developed successfully from L-(-)-menthone.展开更多
As a part of our interest in biologically active germacranolides from the genus Carpesium （Compositae）, we have investigated the constituents of Carpesium cernuum. This paper reports the isolation and structural elu...As a part of our interest in biologically active germacranolides from the genus Carpesium （Compositae）, we have investigated the constituents of Carpesium cernuum. This paper reports the isolation and structural elucidation of a new germacranolide, cernolide A （Compound 1）, from the herb. The structure of Compound 1 was determined as 2α,3β-dihydroxy-9-angeloxygermacra-4-en-6,12-olide on the basis of spectral evidence. The skeleton of Compound 1 was elucidation by IR, MS, ^1H and ^13C NMR, COSY, HMQC and HMBC experiments. The stereochemistry of Compound 1 was deduced by ROESY spectral data. Finally, the procedures of extraction and isolation were described in detail.展开更多
A new flavone glycoside, 5,8-dihydroxy-4',6,7-trimethoxyflavone 8-O-(-D-glucopyranoside 1, together with three known flavonoids, pedalitin 2, cirsimartin 3 and genkwanin 4, were isolated from the aerial parts of I...A new flavone glycoside, 5,8-dihydroxy-4',6,7-trimethoxyflavone 8-O-(-D-glucopyranoside 1, together with three known flavonoids, pedalitin 2, cirsimartin 3 and genkwanin 4, were isolated from the aerial parts of Isodon enanderianus. Their structures were determined on the basis of spectral data.展开更多
A new flavonoid glycoside, 5, 7-dihydroxy-4'-methoxyflavonoid 7-Q-[6-O-(4-O-acetyl-alpha-L-rhamnosyl)-3-O-beta-D-glucosyl]-6-O-acetyl-beta-D-glucoside was isolated from Thalictrum przewalskii. Its structure was de...A new flavonoid glycoside, 5, 7-dihydroxy-4'-methoxyflavonoid 7-Q-[6-O-(4-O-acetyl-alpha-L-rhamnosyl)-3-O-beta-D-glucosyl]-6-O-acetyl-beta-D-glucoside was isolated from Thalictrum przewalskii. Its structure was determined on basis of spectroscopic evidences.展开更多
Objective:To isolate and characterize the cytotoxic compounds from Diospyros quercina(Baill.)G.E.Schatz&Lowry(Ebenaceae).Methods:An ethno-botanical survey was conducted in the south of Madagascar from July to Augu...Objective:To isolate and characterize the cytotoxic compounds from Diospyros quercina(Baill.)G.E.Schatz&Lowry(Ebenaceae).Methods:An ethno-botanical survey was conducted in the south of Madagascar from July to August 2010.Bio-guided fractionation assay was carried out on the root bark of Diospyros quercina,using cytotoxicity bioassay on murine P388 leukemia cell lines as model.The structures of the cytotoxic compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry.Results:Biological experiments resulted in the isolation of three bioactive pure compounds(named TR-21,TR-22,and TR-23)which exhibited very good in vitro cytotoxic activities with the IC_(50)values of(0.017 5±0.0060)μg/mL,(0.089±0.005)μg/mL and(1.027±0.070)μg/mL respectively.Thus,they support the claims of traditional healers and suggest the possible correlation between the chemical composition of this plant and its wide use in Malagasy folk medicine to treat cancer.Conclusions:The ability of isolated compounds in this study to inhibit cell growth may represent a rational explanation for the use of Diospyros quercina root bark in treating cancer by Malagasy traditional healers.Further studies are,therefore,necessary to evaluate the in vivo antineoplastic activity of these cytotoxic compounds as effective anticancer drugs.展开更多
文摘The nuclear factor-KB （NF-KB） transcription factors control many physiological processes including in- flammation, immunity, apoptosis, and angiogenesis. In our search for NF-KB inhibitors from natural resources, we identified 4＇,6-dihydroxy-4-methoxyisoaurone （ISOA） as an inhibitor of NF-KB activation from the seeds of Tricho- santhes kirilowii. However, the mechanism by which ISOA inhibits NF-KB activation is not fully understood. In the present study, we demonstrated the effect of ISOA on NF-KB activation in TNF-α-stimulated HeLa cells. This com- pound suppressed NF-KB activation through the inhibition of IKB kinase （IKK） activation. ISOA also has an influ- ence on upstream signaling of IKK through the inhibition of expression of adaptor proteins, TNF receptor-associated factor 2 （TRAF2） and receptor interacting protein 1 （RIP1）. Consequently, ISOA blocked the phosphorylation and degradation of the inhibitor of NF-KB alpha （IKBα） , and subsequent phosphorylation and nuclear translocation of p65. The suppression of NF-KB activation by ISOA led to the down-regulation of target genes involved in inflam- mation, proliferation, angiogenesis and invasion, as well as potentiation of TNF-α-induced apoptosis at least in part through activation of caspase-8. Taken together, this study extends our understanding on the mechanisms underly- ing the anti-inflammatory and anti-cancer activities of ISOA. Our findings provide new insight into the molecular mechanisms and a potential application of ISOA for inflammatory diseases as well as certain cancers associated with abnormal NF-KB activation.
基金partially supported by the fund of Key Laboratory of Marine Drugs(0cean University of China),Ministry of Education[KLMD(0UC)2004]by the National Natural Science Foundation of China(No.30530080)+1 种基金A program supported by the Department of Science and Technology of Shandong Province(No.2006GG2205023)by the Guangdong Key Laboratory of Marine Materia Medica is also gratefully acknowledged.
文摘Cultivation of an endophytic fungus Aspergillus niger EN-13 that was isolated from the inner tissue of the marine brown alga Colpomenia sinuosa resulted in the characterization of a new naphthoquinoneimine derivative, namely, 5,7-dihydroxy-2-[1-（4- methoxy-6-oxo-6H-pyran-2-yl）-2-phenylethylamino]-[ 1,4]naphthoquinone. The structure of the new compound was established on the basis of various NMR spectroscopic analyses including 2D NMR techniques, El-MS, and HR-ESI-MS. This compound displayed moderate antifungal activity.
基金the Natural Science Foundation of Shaanxi Province (No. 2001K11-G5).
文摘Two hydrates of sodium 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Na(H2O)](C17H13O6SO3)2H2O, 1) and nickel 5,7-dihydroxy-6,4'-dimethoxyisoflavone-3'-sulfonate ([Ni(H2O)6](C17H13O6SO3)24H2O, 2) were syn-thesized and characterized by IR, 1H NMR and X-ray diffraction analyses. The hydrate 1 crystallizes in the mono-clinic system, space group P2(1) with a=0.8201(9) nm, b=0.8030(8) nm, c=1.5361(16) nm, =102.052(12), V=0.9893(18) nm3, Dc=1.579 g/cm3, Z=2, =0.252 nm-1, F(000)=488, R=0.0353, wR=0.0873. The hydrate 2 belongs to triclinic system, space group P-1 with a=0.7411(3) nm, b=0.8333(3) nm, c=1.7448(7) nm, a=86.361(6), 撸?6.389(5), ?=88.999(3), V=1.0731(7) nm3, Dc=1.587 g/cm3, Z=1, =0.649 mm-1, F(000)=534. In the structure of 1, the sodium cation is coordinated by six oxygen atoms and two adjacent ones are bridged by three oxygen atoms to form an octahedron chain. The C—H…p hydrogen bonds exist between two isoflavone molecules in the structure of 2. Meanwhile, hydrogen bonds in two compounds, link themselves to assemble two three-dimensional network structures, respectively.
文摘A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.
文摘A new alkaloid, named 6-（2＇,3＇-dihydroxy-4＇-hydroxymethyl-tetrahydro-furan-1＇-yl）cyclopentadiene[c]pyrrole-1,3-diol, was isolated from the seeds of Castanea mollissima Blume. The structure was elucidated based on spectroscopic evidence including 2D NMR techniques.
基金One of the authors(J.Wandji)is grateful for grant(No.F/2624-3F)from the International Foundation for Science(Sweden)the sponsorship of the"UniversitéParis Descartes,France"during his multiple research visits in Paris.
文摘Two new compounds 7-hydroxy-5-O-（β-D-glucopyranoside） flavan （1） and （Z）-4＇,6＇-dihydroxy-2＇-O-（β-D-glucopyranoside） chalcone （2）, along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia （Euphorbiaceae）. Their structures were established on the basis of spectroscopic analysis and chemical evidence.
文摘A convenient and stereoselective approach to the synthesis of(3S. 4R. 6S)- 2-oxo-3, 4-dihydroxy-6-methyl-octanate derivative, a key intermediate for the synthesis of HIV-1 protease inhibitor of didemnaketals analogue, has been developed successfully from L-(-)-menthone.
文摘As a part of our interest in biologically active germacranolides from the genus Carpesium （Compositae）, we have investigated the constituents of Carpesium cernuum. This paper reports the isolation and structural elucidation of a new germacranolide, cernolide A （Compound 1）, from the herb. The structure of Compound 1 was determined as 2α,3β-dihydroxy-9-angeloxygermacra-4-en-6,12-olide on the basis of spectral evidence. The skeleton of Compound 1 was elucidation by IR, MS, ^1H and ^13C NMR, COSY, HMQC and HMBC experiments. The stereochemistry of Compound 1 was deduced by ROESY spectral data. Finally, the procedures of extraction and isolation were described in detail.
文摘A new flavone glycoside, 5,8-dihydroxy-4',6,7-trimethoxyflavone 8-O-(-D-glucopyranoside 1, together with three known flavonoids, pedalitin 2, cirsimartin 3 and genkwanin 4, were isolated from the aerial parts of Isodon enanderianus. Their structures were determined on the basis of spectral data.
文摘A new flavonoid glycoside, 5, 7-dihydroxy-4'-methoxyflavonoid 7-Q-[6-O-(4-O-acetyl-alpha-L-rhamnosyl)-3-O-beta-D-glucosyl]-6-O-acetyl-beta-D-glucoside was isolated from Thalictrum przewalskii. Its structure was determined on basis of spectroscopic evidences.
基金Supported by the Third World Academy of Science.(TWAS Fellowship for Research and Advanced Training FR number:Grant No.3240224121the International Foundation for Science (IFS,Stockholm,Sweden) and the Organizationfor the Prohibition of Chemical Weapons(OPCW)(IFS Research Grant No F/4921-2)
文摘Objective:To isolate and characterize the cytotoxic compounds from Diospyros quercina(Baill.)G.E.Schatz&Lowry(Ebenaceae).Methods:An ethno-botanical survey was conducted in the south of Madagascar from July to August 2010.Bio-guided fractionation assay was carried out on the root bark of Diospyros quercina,using cytotoxicity bioassay on murine P388 leukemia cell lines as model.The structures of the cytotoxic compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry.Results:Biological experiments resulted in the isolation of three bioactive pure compounds(named TR-21,TR-22,and TR-23)which exhibited very good in vitro cytotoxic activities with the IC_(50)values of(0.017 5±0.0060)μg/mL,(0.089±0.005)μg/mL and(1.027±0.070)μg/mL respectively.Thus,they support the claims of traditional healers and suggest the possible correlation between the chemical composition of this plant and its wide use in Malagasy folk medicine to treat cancer.Conclusions:The ability of isolated compounds in this study to inhibit cell growth may represent a rational explanation for the use of Diospyros quercina root bark in treating cancer by Malagasy traditional healers.Further studies are,therefore,necessary to evaluate the in vivo antineoplastic activity of these cytotoxic compounds as effective anticancer drugs.
基金supported financially by the NSFC(Nos. 30830115 and 20902093)the foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China(No.P2008- ZZ13)the Reservation-talent Project of Yunnan Province(No. 2011 CI043)
文摘Received 22 November 2012 Received in revised form 25 December 2012 Accepted 2B December 2012 Available online 4 February 2013
